


Not Even A Finger?

by skyressshun



Category: Supernatural
Genre: Bottom Dean, Dildos, Experienced Castiel, Gay Castiel, Gen, Masturbation, Plot What Plot/Porn Without Plot, Vibrators, dean and lisa relationship - mentioned, dean tries to get himself off, dean's clueless, experimenting dean, hinted bisexual dean, inexperienced dean, like seriously he's clueless
Language: English
Status: Completed
Published: 2017-02-27
Updated: 2017-02-27
Packaged: 2018-09-27 04:46:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,850
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9966002
Author URL: https://archiveofourown.org/users/skyressshun/pseuds/skyressshun
Summary: Dean reveals he's never fingered himself. Cas thinks it's hilarious. So of course Dean's got to try it. How hard can it be right? Hell, he could probably fit a whole dildo up there no problem.





	

This is stupid. It wasn’t too late to back out. He doesn’t even know why he’s doing it. God, it’s all so stupid. He should just put it back before she comes back from the bathroom. But he can’t. He’s already this far, what’s a little further.

So with great hesitance Dean slides his girlfriend of two years vibrator into his school bag and zips it shut. He can feel his heart racing, anxiety coursing through him. What if she wants to use it tonight? What if they have sex and she goes rooting through his bag for a condom and finds it? What if-

His long tirade of questions is shut off by Lisa’s return, her long dark hair pulled back into a bun and her shirt rumpled slightly. She’s smiling far too seductively for someone who just came back from the toilet to change her tampon. (Apparently two years is the time all barriers disappear in a relationship). Dropping besides him her delicate hands cup his jaw and pull him into a slow and easy kiss. Their mouths melding together easily and with obvious familiarity.

“I’d ask you to spend the night but my cramps are killing me,” she mumbles against his lips, swiping her tongue out to taste him.

“Don’t worry about it, I’ll be out of your hair soon. Do you, uh, want me to get you some pain pills or something?” He tried to hide his relief that sex was off the table and was glad that his voice came out like a concerned boyfriend not a panicking thief. (‘Not thief borrower’ he continuously reminded himself)

“Nah that’s fine babe. I’m probs just gonna sleep, y’know. Besides pills make me sick. Go home, thanks for the lift though.” Another kiss was shared between them before she flops back onto the bed, hands settling on her stomach protectively.

“Okay, I’ll uh call you later, yeah?”

“Yeah fine,”

Grabbing his bag Dean tried not to look too eager slipping from the room, pulling the door closed behind him and letting out a long held in sigh of relief. Shouldering his vibrator hiding bag he padded downstairs and left the silent house, eyes falling of Baby sitting in the drive.

The drive home lasted far too long but was also over startlingly quick. Thankfully the place was empty, Sammy staying over at Kevin’s for a movie marathon and study sesh (geez does the kid ever relax?) and dad hold up in some skeevy bar or thrown in the drunk tank. Either way he wouldn’t be home tonight.

Which meant Dean had complete privacy. And also no excuse to delay what had been eating at him for weeks now.

It was stupid. He’d been sitting at lunch with Cas and the topic of sex came around as it does frequently around teenage boys. Cas had been talking about his latest fling with a British guy called Balthazar (yes that’s his real name) and how the man had admitted to never having bottomed before because ‘seriously what guy hasn’t at least stuck a finger up there’. Dean’s answering splutter had been more than enough for Cas.

_ “Seriously never even a finger?” He’d asked, looking at Dean as though he’d grown a second head. Far too embarrassed to answer the blond hid his face behind his drink and shook his head. God only Cas could make him embarrassed about never fingering himself. “Dude, Dean, you gotta try. Why do you think gays like sex so much? It’s where our fucking G-spot is for God’s sake.” _

The conversation was pretty much over after that but the thought kept niggling in the back of his mind. Was it weird he’d never tried it? Cas certainly thought so, but then again most of his male friends were gay. He’d even thought Dean was at first. (Just ‘cause he has the occasional sexy dream with him Dr Sexy and Dr Sexy’s cowboy boots doesn’t mean anything).

The conversation had to have been a month ago now, and ever since then whenever he was around Lisa and they were having sex, or whenever she played with herself and let him watch he couldn’t help wonder what it would feel like if someone did it to him. And that one time last week where she’d let him put a finger in her arsehole while he ate her out hadn’t done anything to ease his curiosity.

Today he’d finally decided was the time to act. So he’d graciously offered her a ride home and had even carried her bags up to her bedroom. Taking the opportunity as soon as she left the room to rifle around in her bedside drawers, pushing aside the box of tampons and the smaller box of condoms and lifting her lacy panties up to find the bright pink vibrator with a small nub on the end to stimulate her clit. He wasn’t exactly sure what he was meant to do with that seeing as he didn’t have one but he’d figure it out when the time came.

Without having registered even leaving the car Dean found himself in his room with the door closed and locked behind him. Dumping his bag on his bed he flicked on the bedside lamp and closed the curtains, emptying the contents of his bag on the floor and barely holding in a gasp as the dildo dropped out, bouncing slightly on the bare wood.

It looked so much bigger than he remembered, definitely longer than him, and thicker, the pink length ridged with small nodules that vibrated and trembled when turned on. The small protrusion where the clit stimulant was looking incredibly intimidating.

Grabbing it with shaky hands he sat on his bed, saliva feeling too thick in his mouth as he struggled to swallow. Anxiety was pooling in his belly but he couldn’t deny the anticipation melding in there too. He had the strangest need to lean forwards and lick the tip. Holding himself back he set it on his pillow carefully, as though it was a loaded bomb, and started to remove his clothes.

Never had he been more aware of just how many layers he wore.

His boxers were the last to go, his fingers trembling as he let them fall to the floor on the pile of other discarded clothing.

Picking the vibrator back up he laid back on his bed, pulling his pillows up to lean against the headboard. Cautiously he slid his hands over the pink thing, feeling all the lumps and bumps, his breath speeding up and his cock twitching with interest. He hadn’t even noticed he was half-hard, his dick twitching interestedly as he continued to familiarise himself with the fake dick.

His fingers fumbled over the power switch and with a startled yelp he dropped it to the bed, watching as it vibrated in place, pink appendage twitching while the clit stub hummed loudly. It took a whole ten seconds for the shock to subside before he managed to turn it off and lift it to his face again. Green eyes flicked to his own bedside cabinet knowing he had some lube and condoms in there for when Lisa spent the night.

Briefly wondering if this dick would need one he shoved the idea aside, silently cursing himself. Of course it wasn’t it’s not like it could get him pregnant. A dark flush spread across his cheeks, highlighting the speckle of freckles along the bridge of his nose and his cheeks.

Shifting his body he pulled his legs up higher, letting them flop out and expose himself to the slight chill in the air. Settling the tip to his tight, clenched hole he took a deep breath, already having decided he’d shove the whole thing in at once and deal with the consequences later.

“Okay....okay, on three.” His fingers trembled as they held onto the thick cock, telling himself over and over that if Cas could do this then so could he. “1...2...3!”

A sharp cry of pain tore from his lips as he crumpled onto his side, legs shaking as pain rippled through his body, the tip of the cock barely even past his rim. Panicking at the sharp onslaught of pain he ripped it from his body, his hole protesting the rough treatment. It felt as though he’d been tore and tentative fingers brushed over his abused hole only to come back clear.

Okay so no tearing but  _ fuck  _ was that horrible.

Tears prickled at his eyes as he took long deep breaths, trying to will away the pain and embarrassment.

Several minutes passed before he flopped onto his back and took the vibrator in his hands again. He debated calling Cas to ask for advice but decided against it, knowing he’d receive a barking laugh before he hung up on him. Instead he consulted the internet. 

After another few minutes reading everything he could get his hands on he could feel his embarrassment come back full force. God he was such an idiot.

Fumbling in his cabinet he pulled out the partially used lube and a condom (just in case). Smearing a liberal amount across three of his fingers Dean got himself back into position, his erection, unsurprisingly, having flagged since his failed first attempt.

Rubbing his fingers together to warm the cool lube up he slipped his finger down under his balls, across his perineum and over his tight, puffy, hole. A sharp gasp was pulled from his lips, the sensation nothing like he’d expected, it felt good and he wasn’t even inside yet. Deciding the slower approach was best he traced his rim, applying a small amount of pressure, teasing his hole instead of butchering it. With each trace he applied more pressure, the tip of his finger slipping further and further inside before it was in to the first knuckle.

He stilled, giving his body time to adjust to the odd sensation. Not bad. Just odd.

His dick was already twitching with interest as he slowly pressed further in, his finger slipping millimetre by millimetre until he was past the second knuckle and still going. Soft mewls were pulled from tightly closed lips as Dean slowly pushed and pulled his finger. Each long thrust going easier than the last. 

Pulling out ‘til just the tip remained in he pushed back in, a second finger following and stretching his hole out far more than he’d expected. It took long seconds of twisting and flexing his fingers before his ring gave and let him slide in further, brushing over his walls and filling him up beautifully.

A long breathy moan left his lips as he scissored his fingers, back arching whenever he passed over a particularly sensitive spot. Pressing his fingertips up against his insides he dragged them down and out slowly, a loud gasp being pulled from his lips when he ghosted over something, electricity lighting up his nerve endings and leaving him breathless.

“Oh-so t-that’s the G-spot,” he mumbled to no one in particular, pressing over it again before withdrawing his fingers to add a third. Thankfully it slipped in far easier than the previous two and he could feel his body shift with anticipation, his dick fully hard and a wonderful sense of being full taking over and leaving him moaning.

If three fingers felt this good what would the dildo feel like. Tempted to try again he stilled as the memory of the pain flashed through his head. ‘No,’ he thought ‘I’m not making the same mistake twice.’

It took moments before three fingers were easily slipping in and out of his lubed hole and he was more than ready to feel the dildo stretch him out.

Grasping the vibrator with his free hand he carefully withdrew his fingers, hissing at the cold air assaulting his hole and the horrible feeling of being empty.he took the still open tube of lube and squeezed out a large dollop on top, wrapping his hand around it before dragging it down as though he were giving it a very timid, very unsure handjob.

Sure he’d done it to himself dozens of times but it felt weird doing to something else, especially something not attached to a living body.

Hesitantly he reached for the condom he’d took out earlier, ripping the package in half with his teeth before sliding it down his cock with a hiss. He’d done this every time he’d whacked one off not in the shower, not feeling like using a sock for cleanup afterwards. Reasoning with himself that this was the same, and with his hand not in the way there’d probably be more cleanup needed afterwards.

Settling the slick tip to his loose hole he pressed in, slowly this time. As bad as it had felt before was as good it felt now. He could feel his hole stretch around the head, but the burn only sent pleasant shots down to his dick instead of burning pain. Taking long deep breaths he continued to press in, feeling it slide and pull at his insides, mewls escaping before he even realised he was making them. Stopping only when he felt the tip of the protrusion touch his perineum.

He gave a few slow lazy pulls before setting an even pace. Moaning every time it brushed over his prostate, light flashing behind his eyes as sparks were let loose around his body. He was enjoying himself so much he barely realised he wasn’t fully utilising the toy, only noticing when his thumb brushed over the switch.

Opening his eyes he glanced down between his spread legs, tugging them up and pulling them further apart, watching with rapt interest as he penetrated his own body. Taking the plunge he flipped the switch and damn near screamed as pleasure rocked through him, hips jerking uncontrollably and head thrown back as he gasped and groaned trying to keep his hand moving.

“O-oh, oh-God, God-oh-God-yes, ummm, yesss…”

His free hand clutching the back of a trembling thigh he pulled it up, pressing the sensitive skin against his chest and over a pebbled nipple, hissing at the barely there friction. With the new angle he could thrust harder into himself, gasping at easy vibration and whimpering when he ghosted over his prostate. Each full push in causing his back to arch as the vibrating clit bit stimulated his prostate from the outside.

Sure he was going insane Dean dug his nails painfully into his tender thigh, leaving crescent moons indented into his flesh. The pain grounding him slightly whilst also adding another layer onto the pleasure currently wracking his body.

Meeting each thrust of his hand with a bucking of his hips he quickened his pace, heat coiling in his belly and sweat prickling at his forehead. He could feel his balls bunching up as he ground down against the dildo, biting harshly at the inside of his cheek to keep from crying out. The more the pressure built the harder that task was becoming.

His cock was painfully hard, red and twitching as he leaked pre-cum into the condom’s tip. He knew just one touch and he’d be cumming but he couldn’t pry his fingers from the meat of his leg. An impossible task in his hazy lust filled mind.

With one deep hard thrust he angled the vibrator into his prostate, pressing ‘til he’d filled himself completely and the nub pressed in on the outside too. The prolonged onslaught of pleasure finally pushed him over the edge and with a strangled cry verging on a sob he came hard into the condom. Legs trembling and arms losing all their strength as wave after wave of unbelievable sensations wrecked him.

The still vibrating dick worked him through his orgasm, a genuine cry leaving him as he pushed through pleasure straight into oversensitivity. Using what little strength he had left he withdrew the sloppy pink dick and turned it off, letting it drop onto the bed and roll off somewhere.

Taking deep breaths he willed his heart to slow, wincing as he pulled his fingers out of his flesh, sure, even with his barely focusing eye, that he could see red taint his nails.

Too tired to care he flopped back, all his muscles relaxing as the final trembles of his orgasm passed through his body.

It took several minutes before he was somewhat coherent again, and by then his limp cock had discarded the condom itself. The soiled rubber hanging onto the tip by a fraction between his legs. Grimacing at the disgusting state of his cock, slippery with pre-cum and drying cum stains dribbling into the mess of pubes at the base, he tugged it off the final bit, tying a lazy knot in the end before tossing it onto his bedside drawer. He could deal with that later when he wasn’t feeling so damn floaty.

He was going to have to ask Cas about this on their next moving night marathon. Embarrassment be damned he wanted to know  _ everything _ .


End file.
